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Hydrochloric Acid → 6-chloro-7-(2-chloro-4,5-dimethylphenoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid

HRID 855006
Notes
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Reaction equation

HRID 855006 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([CH3:20])=[CH:15][C:14]=1[Cl:21])[O:8][CH:7]([C:22]([F:25])([F:24])[F:23])[C:6]([C:26]([O:28]CC)=[O:27])=[CH:5]2.O.[OH-].[Li+].[Al].Cl>C(OCC)C.C1COCC1.CO.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([CH3:20])=[CH:15][C:14]=1[Cl:21])[O:8][CH:7]([C:22]([F:24])([F:25])[F:23])[C:6]([C:26]([OH:28])=[O:27])=[CH:5]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 5359268AluminumHCID 69518202ethyl 6-chloro-7-(2-chloro-4,5-dimethylphenoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 114873096-chloro-7-(2-chloro-4,5-dimethylphenoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acidYield 34.6%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To the concd product of step 1 in a suitable vial was added 400 mg (mmole) of lithium hydroxide monohydrate, 1 mL of water, 2 mL of methanol and 7 mL of THF. The vial was capped, in an aluminum heating block and the block heated to 100° C. for 30 min. After allowing the vial to cool to rt, the mixture was treated with 5 mL of 1N HCl and 2 mL of diethyl ether. The organic layer was removed and the aqueous layer extracted two times with diethyl ether. Combined organic extracts were concd by evaporation of solvent under a stream of N2 followed by conc in vacuo to afford 150 mg (34.6%) of a yellow solid: 1H NMR (CDCl3/300 MHz) 2.26 (s, 3H), 5.64 (q, 1H, J=6.8 Hz), 6.27 (s, 1H), 6.94 (s, 1H), 7.26 (s, 1H), 7.3H (s, 1H), 11.28 (hs, 1H); MS (ES−) 431 (M−1, 100); HRMS (ES−) m/z calcd for (M−H; C19H12Cl2F3O4) 431.0059, found 431.0048.

Workup

  1. temperatureto cool to rt
  2. customThe organic layer was removed
  3. extractionthe aqueous layer extracted two times with diethyl ether
  4. customCombined organic extracts were concd by evaporation of solvent under a stream of N2

Sources & evidence

ORD record
ord-f034ea96a5b345dea9a765ca46c4cf98
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07259266B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes